Substituted sulfanilyl sulfilimine compounds as herbicides

ABSTRACT

The present invention is directed to novel compounds of the formula   which compounds are useful as herbicides. In the above and succeeding formulae herein, R1 represents hydrogen or R2, and each R2 independently represents loweralkyl of C1-C4, loweralkenyl of C3-C4, loweralkynyl of C3-C4, or radical of the formula -CH2-CH2-CH2-nY wherein n represents 0 or 1, and Y represents methoxy, cyano, bromo, or chloro, subject to the limitation that the groups represented by R1 and R2 together contain from 2 to 8, both inclusive, carbon atoms; and each R3 is taken separately and independently represents loweralkyl of C1-C3 or phenyl, subject to the limitation that both R3 groups together, do not contain more than 8 carbon atoms, or both R3 groups are taken together, and represent a divalent radical selected from the group consisting of -CH2-2-0 -CH2-2 and -CH2-q wherein q represents 4, 5, or 6.

United States Patent [1 1 Beck 14 1 Sept. 30, 1975 1 SUBSTITUTEDSULFANILYL SULFILIMINE COMPOUNDS AS I-IERBICIDES [75] Inventor: James R.Beck, Indianapolis, Ind.

[73] Assignee: Eli Lilly and Company, Indianapolis,

Ind.

22 Filed: July 13, 1973 21 Appl.No.: 379,035

[52] U.S. Cl 71/90; 71/103 51 1m. (31. ..A01N 9 12 [58] Field of Search71/103, 88, 95, 94, 9O

[56] References Cited UNITED STATES PATENTS 3,367,949 2/1968 Soper260/397.7

3,471,436 10/1969 Collins 260/3977 3,542,865 11/1970 Bayer 71/1183,681,406 8/1972 Beck 71/103 3,686,230 8/1972 Moranetz 260/34773,746,727 7/1973 Pilgnam et a1. 71/103 OTHER PUBLICATIONS Tsygarov eta1., Chem. Abst., 41:5687, 9/47. Andus et al., Chem. Abs., 42:4238,6/48. Mongenot et al., Chem. Abs., 3812693, 6/44. Twai et al., Chem.Abs., 582881, 1/63.

Primary ExuminerJames 0. Thomas, Jr. Attorney, Agent, or Firm KathleenR. S. Page; Everet F. Smith [5 7 ABSTRACT The present invention isdirected to novel compounds of the formula which compounds are useful asherbicides. In the above and succeeding formulae herein, R representshydrogen or R and each R independently represents loweralkyl of C,Cloweralkenyl of C -C loweralkynyl of C C,, or radical of the formula CHC1-1- +C1-I +,,Y wherein n represents 0 or 1, and Y represents methoxy,cyano, bromo, or chloro, subject to the limitation that the groupsrepresented by R and R together contain from 2 to 8, both inclusive,carbon atoms; and each R is taken separately and independentlyrepresents loweralkyl of C ,-C or phenyl, subject to the limitation thatboth R groups together, do not contain more than 8 carbon atoms, or bothR groups are taken together, and represent a divalent radical selectedfrom the group consisting of 1-CH- -O +CH and +C1-I- wherein qrepresents 4, 5, or 6.

11 Claims, N0 Drawings SUBSTITUTED SULFANILYL SULFILIMINE COMPOUNDS ASHERBICIDES CROSS REFERENCE TO RELATED APPLICATION This is a division ofmy copending application Ser. No. 183,644, filed Sept. 24, 1971, andissued Jan. 15, 1974, as 3,786,048.

DETAILED DESCRIPTION OF THE INVENTION The present invention is directedto compounds of the formula with a sulfoxide of the formula O -S\R3 inthe presence of a dehydrating agent. The reactants are preferablycontacted in an inert liquid as reaction medium and at refluxtemperatures. Separation, and, if desired, purification, are carried outin conventional procedures.

The compounds of the present invention are named herein as substitutedsulfilimine compounds. The name sulfilimine designates a hypotheticalcompound of the formula HN=SH Compounds comprising the N=S structure, asthe compounds of the present invention, are named .as N- andS,S-derivatives of sulfilimine.

The following examples illustrate the present invention and will enablethose skilled in the art to synthesize all of the compounds of thepresent invention.

EXAMPLE 1: S,S-DIMETHYL-N-( 3,5-DINITRO-N,N-DIPROPYLSULFANILYL)-SULFILIMINE 3 ,5-Dinitro-N ,N-dipropylsulfanilamide(3.5 grams), dimethylsulfoxide (2 milliliters), chloroform (75milliliters) and acetic anhydride (l0 milliliters) were mixed, heated toreflux, and refluxed for 31 hours. Solvent was then removed byevaporation, yielding the desired S,S-dimethyl-N-(3,5-dinitro-N,N-dipropylsulfanilyl)sulfilimine. It was recrystallized twice fromethanol, m.p., l4850C.

Analysis, Calc: C, 41.25; H, 5.44; N, 13.60.

Found: C, 41.38; H, 5.46; N, 13.79.

EXAMPLES 2-10 Other representative compounds of the present invention,prepared in accordance with the foregoing teachings and examples, arethe following:

S ,S-Tetramethylene-N-( 3,5-dinitro-N,N-dipropylsulfanilyl)-su1filimine, m.p., l35-7C., preparedfrom 3,5-dinitro-N ,N-dipropylsulfanilamide and tetrahydrothiopheneoxide.

S,S-Diethyl-N-(3,5-dinitro-N,N-dipropylsulfanilyl)sulfilimine, m.p.,l389C., prepared by reacting 3,5- dinitro-N ,N -dipropylsulfanilamideand diethyl sulfoxide.

S,S-Dipr0pyl-N-( 3 ,5 -dinitro-N ,N-dipropylsulfanilyl sulfilimine,m.p., l002C., prepared by reacting 3,- 5-dinitro-N,N-dipropylsulfanilamide and dipropyl sulfoxide.

S-Ethyl-S-methyl-N-( 3 ,5 -dinitro-N ,N-dipropylsulfanilyl)-sulfilimine,m.p., 103C., prepared by reacting 3,S-dinitro-N,N -dipropylsulfanilamideand ethyl methyl sulfoxide.

S,S-Dimethyl-N-( 3 ,5-dinitro-N-butyl-N-ethylsulfanilyl)-sulfilimine,m.p., l l46C., prepared by reacting 3,5-dinitro-N-buty1-N-ethylsulfanilamide with dimethyl sulfoxide.

S,S-( 3-Oxapentamethylene)-N-( 3 ,5-dinitro-N,N-

dipropylsulfanilyl)-sulfilimine, m.p., l0l3C., prepared by reacting3,5-dinitro-N,N dipropylsulfanilamide with 1,4-oxathiane oxide.

S,S-Pentamethylene-N-(3,5-dinitro-N,N-dipropylsulfanilyl)-sulfilimine,m.p., l079C., prepared by reacting 3,5-dinitro-N ,N-dipropylsulfanilamide with tetrahydrothiopyran oxide.

S,S-Hexamethylene-N-(3,5-dinitro-N,N-dipropylsulfanilyl)-sulfilimine,m.p., l03-5C., prepared by reacting 3,S-dinitro-N,N-dipropylsulfanilamide with thiepane oxide.

S-Methyl-S-phenyl-N-(3,5-dinitro-N,N-dipropylsulfanilyl)-sulfilimine,m.p., l357C., prepared by reacting 3,5-dinitro-N,N-dipropylsulfanilamide with methyl phenyl sulfoxide.

EXAMPLES 11-19:

Yet other representative compounds of the present invention include thefollowing: S,S-Dimethyl-N-(3,5-dinitro-N,N-bis(2-methoxyethyl)sulfanilyl)-sulfilimine S,S-Pentamethylene-N-( 3,5-dinitro-N-isopropylsulfanilyl)-sulfilimineS,S-Diethyl-N-(3,5-dinitro-N,N-bis(2-cyanoethyl)sulfanilyl)-sulfilimineS,S-Tctramethylene-N-( 3,S-dinitro-N,N-dipropynylsulfanilyl)-sulfilimine S-Methyl-S-propyl-N-( 3 ,S-dinitro-N ,N-bis( 2-chloroethyl )sulfanily] )-sulfilimine S,S-Dipropyl-N-( 3,5-dinitro-N,N-bis( 3- bromopropyl )sulfanilyl )-sulfilimine 4S,S-(3-oxapentamethylene)-N-(3,5-dinitro-N,N-

dibutylsulfanilyl)-sulfilimine S-Ethyl-S-propyl-N-( 3 ,5-dinitro-N,N-dipropylsulfanilyl)sulfilimine S,S-Tetramethylene-N-( 3,5-dinitro-N,N-diallylsulfanilyl )-sulfilimine The compounds of thepresent invention are adapted to be employed as herbicides. Thecompounds can be utilized to achieve broad herbicidal action; hence, inits broadest sense, the present invention is directed to a method whichcomprises applying to a plant part, which can be a stern, leaf, flower,fruit, root, or seed or other similar reproductive unit of a plant, agrowthinhibiting amount of one of the compounds of the presentinvention. However, the compounds can also be utilized to take advantageof selective patterns of herbicidal activity.

It is not critical to the practice of the present invention thatcomplete destruction of undesirable vegetation be obtained, it beingadequate if the growth of the unwanted vegetation is merely inhibited.Especially where selective action is sought, inhibition falling short ofactual killing is adequate, particularly when combined with naturallyoccurring conditions such as limited moisture and the like which moreadversely affect the vegetation selectively inhibited than the cropplant.

The compounds of the present invention are suited to a wide variety ofherbicidal applications. Thus, for example, at rates which evoke theselective action of the compounds, which rates are defined morecompletely hereinbelow, the compounds can be used as selectiveherbicides in crop plants, such as, for example, cotton, corn, sorghum,soybeans, wheat, barley, and the like. In such use, application can bemade preemergent to both crops and weeds, or, preferably by means of adirected spray application technique, postemergent to the crop plant butboth preemergent and postemergent to the weeds. In another application,the compounds can be used to give broad herbicidal action on noncropland, including intermittently non-crop strips of contour-farmed land.For such usage on so-called fallow land, application can be made inspring to suppress vegetative growth until a fall or following springplanting, or in the fall to suppress vegetative growth until a spring orfollowing fall planting. Furthermore, in an other application, thepresent compounds can be utilized to control weeds in tree cropplantings, such as plantings of the various citrus trees. Also, thecompounds can be used for turf applications. In addition to theforegoing terrestial embodiments, the present compounds can also beutilized as aquatic herbicides.

The practice of the present invention in any of its numerous embodimentscan in some instances be carried out with unmodified compound; however,for good results, it is generally necessary that the compound beemployed in modified form, that is, as one component of a compositionformulated to implement the plant growth-inhibiting effects. Thus, forexample, the active agent can be mixed with water of other liquid orliquids, preferably aided by the usage of a surface active agent. Theactive agent can also be incorporated on a finely divided solid, whichcan be a surface active substance, to yield a wettable powder, which cansubsequently be dispersed in water or other liquid, or incorporated aspart of a dust which can be applied directly. Other methods offormulations are known in the art and can be employed in implementingthe present invention.

In carrying out the novel method of the present invention, the exactamount of the active agent employed is not critical and will vary,depending upon the type of growth-inhibiting effect desired, theidentity of the plants concerned, the particular active agent used,weather conditions, and the like. In general, a broad growth-inhibitingeffect is obtained with rates of from about 8 to pounds or more ofactive agent per acre,

and such rates are suitable and effective for control of vegetativegrowth on fallow land. When it is desired to obtain a selectivegrowth-inhibiting effect on weeds in areas containing crop plants suchas corn, soybeans, and cotton, rates of from 0.25 to about 8 poundsgenerally give good results. When in the typical mode of operation, theactive agent is employed as a composition comprising the agent, theexact concentration of active agent in the composition is not critical,except that the concentration and total amount of formulation employedbe adequate to supply the appropriate amount of active agent on a peracre basis. In general, good results are obtained when employingformulations containing the active agent in a concentration of from 0.5to 10 percent or higher, in the instance of a liquid formulation; and ina concentration of from 1.0 to 5.0 percent or higher, in the instance ofa dust, powder, granule, or the like. More concentrated formulations canbe prepared and are often preferred in that they can serve, dependingupon the particular application contemplated and the particularconcentration, both as a concentrated formulation for purposes ofshipment, storage, and the like, and as an ultimate treatingcomposition. Thus, for example, formulations often preferably contain asurface active agent and the present active agent; the latter beingpresent in an amount of from 0.5 to 99.5 percent, by weight; or aninert, finely divided solid and the present active agent, the latterbeing present in an amount of from 1.0 to 99.0 percent, by weight. Suchformulations, as indicated, can be employed directly in certainapplications, but can also be diluted and subsequently employed in manyother applications.

Liquid compositions containing the desired amount of active agent areprepared by dissolving the substance in a liquid, with or without theaid of a surface active dispersing agent such as an ionic or non-ionicemulsifying agent. Suitable liquids include agricultural spray oils andthe petroleum distillates such as diesel fuel, kerosene, fuel oilnaphthas and Stoddard solvent. The choice of dispersing and emulsifyingagent and the amount thereof employed is dictated by the nature of thecomposition and by the ability of the agent to facilitate the'dispersion of the active agent in the carrier to produce the desiredcomposition. Dispersing and emulsifying agents which can be employed inthe compositions include the condensation products of alkylene oxideswith phenols and organic acids, alkyl aryl sulfonates, polyoxyalkylenederivatives or sorbitan esters, complex ether alcohols, and the like.Representative surface active agents which are suitably employed inimplementing the present invention are identified in U.S. Pat. No.3,095,299, second column, lines 2536, U.S. Pat. No. 2,655,447, column 5,and U.S. Pat. No. 2,412,510, columns 4 and 5.

In the preparation of dust compositions, the active ingredient isintimately dispersed in and on a finely divided solid such as clay,talc, chalk, gypsum, limestone, vermiculite fines, perlite, and thelike. In one method of achieving such dispersion, the finely dividedcarrier is mechanically mixed or ground with the active agent.

Similarly, dust compositions containing the toxicant compounds can beprepared with various of the solid surface active dispersing agents suchas bentonite, fullers earth, attapulgite and other clays. Depending uponthe proportions of ingredients, these dust compositions can be employedas concentrates and subsequently diluted with additional solid surfaceactive dispersing agents or with chalk, talc, or gypsum and the like toobtain the desired amount of active ingredient in a com-- positionadapted to be employed for the suppression of the growth of the plants.Also, such dust compositions can be dispersed in water, with or withoutthe aid of a. dispersing agent, to form spray mixtures.

Formulations containing the present active agent are oftenadvantageously further modified by incorporation therein of an effectiveamount of a surfactant which facilitates the dispersion and spreading ofthe formulation on the plant leaf surfaces and the incorporation of theformulation by the plant.

In accordance with the present invention, the active agent can bedispersed in soil or other growth media in any convenient fashion.Applications can be carried out by simply mixing with the media, byapplying to the surface of soil and thereafter dragging or discing intothe soil to the desired depth, or by employing a liquid carrier toaccomplish the penetration and impregnation. The application of sprayand dust compositions to the surface of soil, or to plant parts or theabove ground surfaces of plants can be carried out by conventionalmethods, e.g., power dusters, boom and hand sprayers and spray dusters,whether surface or air-borne.

In a further method, the distribution of the active agent in soil can beaccomplished by introducing the agent into the water employed toirrigate the soil. In such procedures, the amount of water is variedwith the porosity and water holding capacity of the soil to obtain adesired depth of distribution of the agent.

In addition, the present method also comprehends the employment of anaerosol composition containing one or more of the present active agentsas an active compound. Such a composition is prepared according toconventional metehods wherein the agent is dispersed in a solvent, andthe resultant dispersion mixed with a propellant in liquid state. Suchvariables as the particular agent to be used and the nature of thevegetation which is to be treated will determine the desirability of thesolvent and concentration of the agent therein.

Satisfactory results are obtained when the active agent of the presentinvention, or a composition comprising such active agent, is combinedwith other agricultural materials intended to be applied to plants,plant parts, or their habitats. Such materials include fertilizers,fungicides, nematocides, insecticides, other herbicides, soilconditioning agents, and the like.

EXAMPLE 20 The formulation of the compounds of the present invention forthe purpose of conducting the herbicidal evaluations, the results ofwhich are reported hereinbelow, was carried out in accordance withconventional procedures. Typically the compound to be evaluated wasinitially suspended in a 1:1 acetone/ethanol solution of a blend ofnonionic sulfonate emulsifying agents. The suspension was then dilutedwith an aqueous solution of the same blend of agents to obtain theultimate treating composition; this composition contained 4.15 percentof each of the acetone and ethanol, 1000 ppm. of the blend ofemulsifying agents, and the respective compounds in an amount to supplythe desired pounds per acre. In the instance of some of the lower rates,a formulation so obtained was further diluted with water containing 1000ppm. of the blend of emulsifying agents, only, thus further lesseningthe concentration of the ethanol and acetone.

EXAMPLES 2 l28 Various of the compounds of the present invention wereevaluated for preemergent application to various species of plants. Inthis evaluation, a soil was prepared consisting of one part masonry sandand one part shredded top soil blended together in a cement mixer. Onegallon of this soil was placed in a 21.5 X 31.5 cm. galvanized flat andwas patted down with a bench brush until level. A three-row marker wasused to make 2 /2 cm. deep furrows in approximately two-fifths of theflat. Crop seeds consisting of four kernels of corn, five cotton seedsand five soybean seeds were placed in these furrows. A template was thenplaced on the remaining soil and the indicated approximate numbers ofeach of the following seeds were planted, one species to each section:foxtail (millet), -100 seeds; rough pigweed (150-250 seeds); and largecrabgrass (-150 seeds).

Sufficient soil was added to cover the entire flat. Thus, the weed seedswere covered to a depth of about 6 mm. and the crop seeds were coveredto a depth of about 3 cm.

In assaying the effect of the composition as preemergent herbicides, aflat prepared as above, taken either on the day of planting or on thenext day, was placed in a chamber equipped with a turntable and an airexhaust. A herbicidal composition containing the subject compound andprepared as described in the preceding example was applied to the flatwith a modified DeVilbiss atomizer hooked to an air source. Twelve andonehalf milliliters of the composition under test were applied to eachflat either on the day of planting or the succeeding day. Injury ratingsand observations as to type of injury were made 1 l to 12 days aftertreatment. The injury rating scale used was as follows:

0no injury lslight injury 2-moderate injury 3severe injury 4-death Whenmore than one determination was carried out at a given rate, an averagevalue was calculated for the injury rating.

In the following table setting forth the results of the evaluation,column 1 gives the name of the compound under test; column 2, the ratein pounds per acre at which the compound was applied to the test flat;and the remaining columns, the injury to the particular plant seeds orseedlings as measured by the foregoing scale.

TABLE 1 Injury Rating on Preemergent Treatment Lbs./

Compound Acre Corn Cotton Soybean Crabgrass Pigweed FoxtailS,SDimethyl-N-( 3,5-dinitro- 8 2 2 2 4 4 4 N,Ndipropylsulfanilyl)sulfilimine 4 0 0 0 3 3 3 TABLE l-Continued lnjury Rating on PreemergentTreatment Lbs./

Compound Acre Corn Cotton Soybean Crabgrass Pigweed FoxtailS,S-Tctramethylene-N-( 3 ,5- 8 O O 0 4 4 3dinitro-N,N-dipropylsulfanilyl)sulfilimine 4 l O 3 4 3 2 l 0 3 3.5 3S,S-Diethyl-N-(3,5-dinitro- 8 0 3 0 3 N,N-dipropylsulfanilyl)-sulfilimine 4 O 0 0 2 O 3 S,S-Dipropyl-N-(3,5-dinitro- 8 l 3 0 3N,N-dipropylsulfanilyl)- sulfilimine 4 0 0 0 3 0 2S-Ethyl-S-methyl-N-(3,5- 8 2 3 2 3dinitro-N,N-dipropylsulfanilyl)sulfilimine 4 l 0 O 3 2 2S,S(3-Oxapentamethylcne)- 8 2 4 l 3 N-(3,5dinitro-N,N-dipropylsulfanilyly 4 2 O 0 3 l 2 sulfilimine S-Methyl-S-phenyl-N-(3,5-8 2 3 2 3 dinitro-N,N-dipropylsulfanilyhsulfilimineS,S-Dimethyl-N-(3,5-dinitro- 8 2 3 3 1 N-butyl-N-ethylsulfanilyl)- 4 l OO 3 3 3 sulfilimine 2 l O 0 3 2 2 EXAMPLES 29-37 wherein R representshydrogen or R each R independently represents loweralkyl of C -C subjectto the limitation that the groups represented by R and R togethercontain from 2 to 8, both inclusive, carbon atoms; and each R is takenseparately and independently represents loweralkyl of C -C or both R aretaken together and represent tetrarnethylene.

Especially preferred compounds are S,S-dimethyl-N-(3,5-clinitro-N,N-dipropylsulfanilyl)sulfilimine and S,S-tetramethylene-N-( 3 ,5-dinitro-N,N-dipropylsulfanilyl)sulfilimine. Eachof these compounds was further evaluated for plant growth control underfield conditions.

EXAMPLES 38-39 In a first series of evaluations, each of S,S-dimethylN-( 3 ,S-dinitro-N ,N-dipropylsulfanilyl )sulfilimine andS,S-tetramethylene-N-(3,5-dinitro-N,N- dipropylsulfanilyl)sulfiliminewas evaluated under field conditions for herbicidal efficacy andtolerance to cotton and soybean. Each of the compounds was formulated asa wettable powder which was then dispersed in water and sprayed ontofield plots one day after the plots had been seeded with cotton andsoybeans and overseeded with foxtail millet, pigweed, ragweed,jimsonweed, velvetleaf, and morning glory. Weather conditions weretypical for the summer season of a north temperate climate. Readingswere made at intervals R4 R6 following application ofthe compounds: forcrop stand count, at 1 1 days followmg application; for crop in ury, R5at 3 and 6 weeks following application; and for weed control, at 4 and 6weeks after application. The results NO were as reported in thefollowing table.

TABLE 2 Percent Crop Percent Reduction l 'u Percent Grass PercentBroadleaf in Crop Stand Cotton Soybean Control Control Compound Lbs./A.Cotton Soybean lst 2nd lst 2nd lst 2nd lst 2nd S,S-Dimethyl-N- 1.0 0 3 00 0 0 80 37 33 47 (3,5 dinitro-N,N- dipropylsulfanilyl)- 2.0 0 5 0 0 0 088 67 63 sulfilimine TABLE 2 Continued Percent Crop Percent ReductionInjury Percent Grass Percent Broadleaf in Crop Stand Cotton SoybeanControl Control Compound Lbs/A. Cotton Soybean lst 2nd 1 st 2nd lst 2ndlst 2nd S,S-Tetramethyll 3 0 O 0 O 72 47 47 40 ene-N-(3,5-dinitro-N,N-dipropylsul- 2 0 5 3 0 0 0 80 70 55 53 fanilyl)sulfilimine 4 0 l4 7O O O 89 87 72 73 8 9 14 3O 2O 3 13 96 90 87 83 (Control) 0 0 0 0 0 o 00 0 o EXAMPLES 40-41 Like evaluations were conducted withS,S-dimethylformula Cl-l -CH -CH -)-,,Y wherein n represents 0 or 1, andY represents methoxy, cyano, bromo, or chloro, subject to the limitationthat the groups reprel5N-(3,5-d1n1tro-N,N-(dipropylsulfanllyl)sulfilimme and sented by R and Rtogether contain from 2 to 8, bothS,S-tetramethylene-N-(3,5-dinitro-N,N-(dipropylsulinclusive, carbonatoms; and each R is taken sepafanilyl)sulfiliamine, except that thecrops were wheat r r ly and independently represent loweralkyl of C -Cand barley and that the rates were cut in half. The reh l bj to h li i ih b h R groups, sults r as set forth n the l ng tabletogether, do notcontain more than 8 carbon atoms, or

TABLE 3 Percent Percent Reduction in Percent Crop Injury PercentBroadleaf Crop Stand Wheat Barley Grass Control Control CompoundLbs./Acre Wheat Barley lst 2nd 3rd lst 2nd 3rd 1st 2nd 3rd lst 2nd 3rdS,S-Dimethyl- 0.5 0 6.9 3 0 3 6 3 3 70 47 35 13 13 0 N-(3,5dinitro-N,N-dipropyl 1.0 9.4 5.9 20 7 17 13 3 10 85 68 57 47 33 12 sulfanilyl)-sulfilimine 2.0 14.5 24.1 43 47 33 27 22 91 82 82 80 57 57 40 34.1 20.060 70 67 36 33 96 97 97 94 70 68 S,S-Tetramethylene-N-(3,5- 0.5 0 2.8 0o o o o o 63 53 33 23 7 0 dinitro-N,N- dipropylsul- 1.0 0 2.8 l0 7 7 l07 5 77 68 49 57 33 37 fanilylJsulfilimine 2.0 l8.6 24.1 26 27 15 33 2722 91 73 73 85 60 50 4.0 16.6 17.0 43 50 33 46 50 45 95 91 89 90 78 80(Control) 0 0 o 0 0 0 0 0 0 0 0 0 o 0 The compounds to be employed asstarting materials both R groups are taken together, and represent adivalent radical selected from the group consisting of -(CH l- O(CH and+CH wherein q represents 4, 5, or 6. O 2. The method of Claim 1 whereinthe active agent is R a compound of the formula are themselves preparedin known procedures, and many of them are commercially available.Typically, the starting materials are prepared by oxidation of thecorresponding sulfides.

I claim: 1. The method suitable for effecting plant growth inhibitionwhich comprises applying to a plant part a growth-inhibiting amount ofan active agent, said active agent being a compound of the formula N02wherein R represents hydrogen or R each R independently representsloweralkyl of C -C subject to the limitation that the groups representedby R and R together contain from 2 to 8, both inclusive, carbon atoms;and each R is taken separately and independently represents loweralkylof C C or both R are taken together and represent tetramethylene.

3. The method of claim 2 wherein the active agent isS,S-dimethyl-N-(3,5-dinitro-N,N-dipropylsulfanilyl)- sulfilimine.

wherein R represents hydrogen or R and each R independently representsloweralkyl of C -C loweralkenyl of C C loweralkynyl of C -C or radicalof the 4. The method of claim 2 wherein the active agent isS,S-tetramethylene-N 3 ,S-dinitro-N ,N-dipropylsulfanilyl)-sulfilimine.

5. The method for controlling weeds in turf which comprises applying tothe turf an amount of active agent which selectively inhibits the growthof only the weeds, said active agent being a compound of the formula 5 NR /N so =s wherein R represents hydrogen or R and each R independentlyrepresents loweralkyl of C -C loweralkenyl of C -C loweralkynyl of C -Cor radical of the formula CH CH -(CH -),,Y wherein n represents or 1,and Y represents methoxy, cyano, bromo, or chloro, subject to thelimitation that the groups represented by R and R together contain from2 to 8, both inclusive, carbon atoms; and each R is taken separately andindependently represent loweralkyl of C -C or phenyl subject to'thelimitation that both R groups, together, do not contain more than 8carbon atoms, or both R groups are taken together, and represent adivalent radical selected from the group consisting of (-CH O(CH andCl-l wherein q represents 4, 5, or 6.

6. The method of claim wherein the active agent is a compound of theformula wherein R represents hydrogen or R each R independentlyrepresent loweralkyl of C -C subject to the limitation that the groupsrepresented by R and R together contain from 2 to 8, both inclusivecarbon atoms; and each R is taken separately and independentlyrepresents loweralkyl of C -C or both R are taken together and representtetramethylene.

7. The method of claim 6 wherein the active agent is S,S-dimethylN(3,5-dinitro-N,N-dipropylsulfanilyl)- sulfilimine.

8. The method of claim 6 wherein the active agent isS,S-tetramethylene-N-(3,S-dinitro-N,N-dipropylsulfanilyl )sulfilimine.

9. The composition suitable for effecting plant growth inhibition whichcomprises a surface active agent and a plant growth inhibiting amount ofan active agent, said active agent being a compound of the formulawherein R represents hydrogen or R and each R independently representsloweralkyl of C C loweralkenyl of C -C loweralkynyl of C -C or radicalof the formula Cl-l Cl-l -(-CH -),,Y wherein n represents 0 or 1, and Yrepresents methoxy, cyano, bromo, or chloro, subject to the limitationthat the groups represented by R and R together contain from 2 to 8,both inclusive, carbon atoms; and each R is taken separately andindependently represents loweralkyl of C C or phenyl subject to thelimitation that both R groups, together, do not contain more than 8carbon atoms, or both R groups are taken together, and represent adivalent radical selected from the group consisting of -(-CH O-(CH and(-CH wherein q represents 4, 5, or 6.

10. The composition of claim 9 wherein the active agent isS,S-dimethyl-N-(3,S-dinitro-N,N-dipropylsulfanilyl)-sulfilimine.

11. The composition of claim 9 wherein the active agent isS,S-tetrametliylene-N-(3,5-dinitro-N,N- dipropylsulfanilyl)-sulfilimine.

1. THE METHOD SUITABLE FOR EFFECTING PLANT GROWTH INHIBITION WHICHCOMPRISES APPLYING TO A PLANT PART A GROWTH-INHIBITING AMOUNT OF ANACTIVE AGENT, SAID ACTIVE AGENT BEING A COMPOUND OF THE FORMULA
 2. Themethod of claim 1 wherein the active agent is a compound of the formula3. The method of claim 2 wherein the active agent isS,S-dimethyl-N-(3,5-dinitro-N,N-dipropylsulfanilyl)sulfilimine.
 4. Themethod of claim 2 wherein the active agent isS,S-tetramethylene-N-(3,5-dinitro-N,N-dipropylsulfanilyl)-sulfilimine.5. The method for controlling weeds in turf which comprises applying tothe turf an amount of active agent which selectively inhibits the growthof only the weeds, said active agent being a compound of the formula 6.The method of claim 5 wherein the active agent is a compound of theformula
 7. The method of claim 6 wherein the active agent isS,S-dimethyl-N-(3,5-dinitro-N,N-dipropylsulfanilyl)sulfilimine.
 8. Themethod of claim 6 wherein the active agent isS,S-tetramethylene-N-(3,5-dinitro-N,N-dipropylsulfanilyl)sulfilimine. 9.The composition suitable for effecting plant growth inhibition whichcomprises a surface active agent and a plant growth inhibiting amount ofan active agent, said active agent being a compound of the formula 10.The composition of claim 9 wherein the active agent isS,S-dimethyl-N-(3,5-dinitro-N,N-dipropylsulfanilyl)-sulfilimine.
 11. Thecomposition of claim 9 wherein the active agent isS,S-tetramethylene-N-(3,5-dinitro-N,N-dipropylsulfanilyl)-sulfilimine.